By Robert Klara

December 19, 2016

Even though nearly four decades have passed, Jane Maas remembers her scariest client as though it were yesterday.

"She was a bully. It was such a torment to work with her," said Maas, who actually used to whisper prayers on her way to meetings, hoping to avoid the forked tongue of her client. "Everybody was afraid of her," Maas adds. "Even her own bodyguard, who'd been a New York City police officer, was afraid of her."

The client? Leona Helmsley.

If you're over 40, a longtime New Yorker or both, that name requires no explanation. The imperious wife of real estate developer Harry Helmsley, Leona—who personally ran six of her husband's opulent Manhattan hotels—was probably the most famous female face of 1980s New York. Much of the reason for that fame was her advertising. Helmsley insisted on appearing in all of her ads, a decision that put her arched eyebrows and crafty smile in newspapers, magazines and on TV for nearly a decade.

Ad exec Jane Maas Investigation Discovery

Leona Helmsley died in 2007, but her face is back on-screen this holiday season. For the second year running, Investigation Discovery has dusted off some old episodes of Barbara Walters Presents featuring the movers and shakers of a generation ago, and Leona Helmsley is one of them.

The episode, "The Queen of the Palace," is what Investigation Discovery group president Henry Schleiff calls "the quintessential example of Barbara's efforts in revealing a woman whose understanding and expertise in branding exceeded even her impressive knowledge of real estate—perhaps creating the template, today, for President-elect Donald Trump." (Hold that thought. We'll come back to it.)

The reappearance of the Walters special, which is also available on demand via Idgo, has put Maas back in the public spotlight, too. No doubt, it'll also win her a new generation of sympathizers. While Helmsley indisputably ran some fine hotels (the portfolio numbered 30 at its peak), she also ran them like Stalin.

Notorious for humiliating her employees and firing them for the smallest infractions, Helmsley was by most accounts the boss from hell. New York Mayor Ed Koch once called her the Wicked Witch of the West, and Helmsley's own attorney conceded she was a "tough bitch."

"A spiteful, extravagant, foul-mouthed woman who terrified her underlings," is how The New York Times sized up Helmsley—in her obituary.

As a general rule, the closer you worked with Helmsley, the more you suffered, meaning Maas suffered more than most. She held down what had to be Madison Avenue's most prestigious yet least desired job: the personal advertising rep for Leona.

The post lasted a mere seven months, but, Maas said, "it was a degrading, terrible seven months."

The groundbreaking ads

Jane Maas first met Leona Helmsley at a party given by then New York Gov. Hugh Carey. As a young executive with Wells Rich Greene, Maas had worked on "I Love New York," the tourism campaign conceived amid the panic of the city's social and fiscal collapse that also yielded Milton Glaser's iconic logo. The mercurial Helmsley had just fired her agency, Berber Silverstein & Partners, (she would wind up firing them four times in total) and was looking for a new ad shop. Maas, who'd just struck out on her own with three employees, got the job.

Maas immediately made the difficult but wise decision to continue with the creative template that the preceding agency had established, one that featured Helmsley (ebullient in cascading ball gowns and her 1980s feathered hair) at the center of all of the ads.